5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine

Base Information

Chemical Name:5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine
CAS No.:278803-36-4
Molecular Formula:C₃₆H₅₃N₅O₄Si₂
Molecular Weight:676.019
Hs Code.:

Synonyms:5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine

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Chemical Property of 5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine

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Technology Process of 5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine

There total 5 articles about 5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

: 100-46-9
benzylamine

: 236427-58-0
2-bromo-6-benzyloxy-9-[2-deoxy-3,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]purine

: 278803-36-4
5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine

Guidance literature:: With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In toluene; at 80 ℃; for 16h;
DOI:10.1016/S0040-4039(00)01196-5

Reference yield:

: 51549-35-0
3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

: 278803-36-4
5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine

Guidance literature:: Multi-step reaction with 3 steps

1: 67 percent / PPh₃; DEAD / dioxane

2: 60 percent / SbBr₃; t-butyl nitrite / various solvent(s) / -10 °C

3: 58 percent / t-BuONa; (R)-(+)-BINAP / Pd₂dba3 / toluene / 0.5 h / 80 °C

With tert.-butylnitrite; antimony(III) bromide; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; sodium t-butanolate; diethylazodicarboxylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; toluene; 1: Alkylation / 2: Substitution / 3: Substitution;
DOI:10.1021/jo991501+

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 278803-36-4
5'-O-3'-O-bis(tert-butyldimethylsilyl)-6-O-benzyl-2-N-benzyl-2'-deoxyguanosine

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / imidazole / dimethylformamide

2: 67 percent / PPh₃; DEAD / dioxane

3: 60 percent / SbBr₃; t-butyl nitrite / various solvent(s) / -10 °C

4: 58 percent / t-BuONa; (R)-(+)-BINAP / Pd₂dba3 / toluene / 0.5 h / 80 °C

With 1H-imidazole; tert.-butylnitrite; antimony(III) bromide; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; sodium t-butanolate; diethylazodicarboxylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: silylation / 2: Alkylation / 3: Substitution / 4: Substitution;
DOI:10.1021/jo991501+